On the edge of downtown is the Sag Harbor Inn (45 W. Water St., 631/725-2949, www.sagharborinn.com , $220–459 in summer, $110–295 off-season, includes breakfast), a modern, two-story hotel with about 40 clean, spacious rooms, many with balconies overlooking the harbor.
Similar in style is the Baron’s Cove Inn (31 W. Water St., 631/725-2100, www.baronscove.com , $190–480 d in summer, $80–280 d off-season), an upscale resort motel with its own marina. All the rooms here have kitchenettes, and some have private balconies. On site is a pool and roof-top sun deck.
In the heart of Sag Harbor  stands its classiest hostelry, the 1846 American Hotel (25 Main St., 631/725-3535, www.theamericanhotel.com , $250–400 in summer, $135–250 off-season), which dates back to the town’s whaling era. Built of red brick with a white porch out front, the hotel is a member of the Historic Hotels of America. Upstairs are eight guest rooms done up in Victorian antiques; downstairs is an acclaimed restaurant.